Potassium Phosphate, Tribasic → HCID 89721854, Verbindung

HRID 2273086Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2273086
[CH2:1]([N:3]1[CH2:9][C:8]([CH3:11])([CH3:10])[O:7][C:6]2[N:12]=[C:13]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][C@@H:25]3[CH3:30])[N:14]=[C:15](OS(C(F)(F)F)(=O)=O)[C:5]=2[C:4]1=[O:31])[CH3:2].[C:32]([O:36][C:37](=[O:55])[NH:38][C:39]1[CH:44]=[CH:43][C:42](B2OC(C)(C)C(C)(C)O2)=[CH:41][C:40]=1[CH3:54])([CH3:35])([CH3:34])[CH3:33].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:32]([O:36][C:37](=[O:55])[NH:38][C:39]1[CH:44]=[CH:43][C:42]([C:15]2[C:5]3[C:4](=[O:31])[N:3]([CH2:1][CH3:2])[CH2:9][C:8]([CH3:11])([CH3:10])[O:7][C:6]=3[N:12]=[C:13]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][C@@H:25]3[CH3:30])[N:14]=2)=[CH:41][C:40]=1[CH3:54])([CH3:33])([CH3:34])[CH3:35]

Komponenten

8

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 53217256tert-Butyl (2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamateHCID 89714687HCID 89714687, Verbindung

Produkt 1

HCID 89721854HCID 89721854, VerbindungAusbeute 110,8 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 1 g (2.13 mmol) of trifluoromethanesulfonic acid 6-ethyl-8,8-dimethyl-2-((S)-3-methylmorpholin-4-yl)-5-oxo-5,6,7,8-tetrahydro-9-oxa-1,3,6-triazabenzocyclohepten-4-yl ester, 711.35 mg (2.13 mmol) of [2-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]carbamic acid tert-butyl ester, 906.25 mg (4.27 mmol) of tribasic potassium phosphate, 149.83 mg (213.47 μmol) of bis(triphenylphosphine)palladium(II) chloride in 10 ml of dioxane and 3 ml of water is heated in a Biotage microwave machine at 100° C. for 30 minutes. The reaction medium is diluted in 250 ml of ethyl acetate and filtered through Celite. The organic phase is dried over MgSO4. The filtrate is evaporated under reduced pressure. The residue is taken up in 30 ml of heptane, brought to reflux and filtered while hot to give 1.24 g of {4-[6-ethyl-8,8-dimethyl-2-((S)-3-methylmorpholin-4-yl)-5-oxo-5,6,7,8-tetrahydro-9-oxa-1,3,6-triaza benzocyclohepten-4-yl]-2-methylphenyl}carbamic acid tert-butyl ester.

Aufarbeitung

  1. filtrationfiltered through Celite
  2. dry with materialThe organic phase is dried over MgSO4
  3. customThe filtrate is evaporated under reduced pressure
  4. temperatureto reflux
  5. filtrationfiltered while hot

Quellen und Nachweise

ORD-Eintrag
ord-f49fbf915c4440c987ff1482d3baf9e6
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09120812B2

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